| CHARLES E SMITH JEWISH DAY SCHOOL OF | Rockville | B200 Education | $40M | 7 |
| NATIONAL FOUNDATION FOR AFFORDABLE | North Bethesda | L99Z Housing & Shelter | $39.8M | 10 |
| THE PARK SCHOOL OF BALTIMORE | Baltimore | B200 Education | $39.8M | 8 |
| ELEVATOR INDUSTRY WORK PRESERVATION | Columbia | — | $39.5M | 18 |
| DIANA DAVIS SPENCER FOUNDATION INC | Bethesda | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $39M | 8 |
| AMERICAN NURSES ASSOCIATION INC | Silver Spring | — | $38.6M | 22 |
| THE ARC MONTGOMERY COUNTY INC | Rockville | — | $38.5M | 5 |
| FRIENDS SCHOOL OF BALTIMORE INC | Baltimore | B200 Education | $38.4M | 6 |
| CHEVY CHASE CLUB INC | Chevy Case | — | $37.9M | 8 |
| HOSPICE OF THE CHESAPEAKE INC | Pasadena | — | $37.8M | 12 |
| THE CHILDREN'S GUILD INC | Baltimore | P300 Human Services | $37.7M | 10 |
| WEST COAST NEONATOLOGY INC | Baltimore | — | $37.7M | 18 |
| FAMILY SERVICES INC | Gaithersburg | P400 Human Services | $37.6M | 9 |
| PLAYERS PHILANTHROPY FUND INC | Towson | T50 Philanthropy, Voluntarism & Grantmaking Foundations | $37.5M | 0 |
| ST ANDREW'S EPISCOPAL SCHOOL INC | Potomac | — | $37.3M | 7 |
| Greater Baden Medical Services Inc | Brandywine | E20Z Health Care | $37.1M | 9 |
| BROADMEAD INC | Cockeysville | P750 Human Services | $37M | 12 |
| ASHLEY INC | Havre De Grace | F220 Mental Health & Crisis Intervention | $36.8M | 12 |
| JEWISH SOCIAL SERVICE AGENCY | Rockville | P200 Human Services | $36.8M | 8 |
| THE FOUNDATION FIGHTING BLINDNESS INC | Columbia | H410 Medical Research | $36.6M | 14 |
| INTERNATIONAL TRAINING FUND | Annapolis | S99 Community Improvement & Capacity Building | $36.6M | 6 |
| GARRISON FOREST SCHOOL INC | Owings Mills | B200 Education | $36.5M | 7 |
| UNIVERSITY OF MARYLAND PEDIATRIC | Baltimore | G98Z Diseases, Disorders & Medical Disciplines | $36.5M | 7 |
| RICHCROFT INC | Hunt Valley | P730 Human Services | $36.5M | 6 |
| INGLESIDE PRESBYTERIAN RETIREMENT | Rockville | P750 Human Services | $36.4M | 11 |
| MANAGEMENT LEADERSHIP FOR TOMORROW | Bethesda | B60Z Education | $36.3M | 8 |
| INT'L ORTHODOX CHRISTIAN CHARITIES INC | Baltimore | Q330 International, Foreign Affairs & National Security | $36.2M | 8 |
| NATIONAL MARINE SANCTUARY FOUNDATION | Silver Spring | C113 Environment | $36M | 9 |
| LIFE & HEALTH INSURANCE GUARANTY | Aberdeen | — | $36M | 1 |
| UNIVERSITY OF MARYLAND DIAGNOSTIC | Baltimore | — | $35.9M | 77 |
| PUBLIC LIBRARY ASSOCIATION OF ANNAPOLIS AND A A CO INC | Annapolis | — | $35.9M | 7 |
| KESWICK MULTI-CARE CENTER INC | Baltimore | — | $35.7M | 10 |
| NATIONAL CENTER ON INSTITUTIONS AND | Baltimore | — | $35.6M | 6 |
| AMERICAN UROLOGICAL ASSOCIATION | Linthicum Hts | H030 Medical Research | $35.4M | 24 |
| ASSOCIATED JEWISH CHARITIES OF BALTIMORE | Baltimore | T700 Philanthropy, Voluntarism & Grantmaking Foundations | $35.3M | 7 |
| AMERICAN YOUTH HOSTELS INC | Silver Spring | L40C Housing & Shelter | $35.3M | 14 |
| CAL RIPKEN SR FOUNDATION INC | Baltimore | B99 Education | $34.9M | 12 |
| SECOND CHANCE INC | Baltimore | J20 Employment | $34.8M | 3 |
| CHIMES METRO INC | Baltimore | P700 Human Services | $34.6M | 7 |
| HOMEWOOD AT HANOVER PA INC | Williamsport | P750 Human Services | $34.5M | 9 |
| CORNERSTONE MONTGOMERY | Rockville | — | $34.4M | 10 |
| POINT BREEZE CREDIT UNION | Hunt Valley | — | $34M | 23 |
| MARYLAND FAMILY NETWORK INC | Baltimore | P40B Human Services | $33.8M | 5 |
| SO WHAT ELSE INC | Bethesda | T40 Philanthropy, Voluntarism & Grantmaking Foundations | $33.8M | 1 |
| CALVERT IMPACT CAPITAL INC | Bethesda | S300 Community Improvement & Capacity Building | $33.4M | 8 |
| THE JUBILEE ASSOCIATION OF MARYLAND INC | Kensington | P700 Human Services | $33.4M | 8 |
| ROCHAMBEAU THE FRENCH INTERNATIONAL | Bethesda | — | $33.4M | 7 |
| CARROLL LUTHERAN VILLAGE INC | Westminster | P750 Human Services | $33.2M | 8 |
| THE MONARCH ACADEMY PUBLIC CHARTER | Baltimore | B29 Education | $33.2M | 2 |
| Oxford House Inc | Silver Spring | — | $32.9M | 2 |
